CA2384407A1 - 2-azapurine compounds and their use - Google Patents

2-azapurine compounds and their use Download PDF

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Publication number
CA2384407A1
CA2384407A1 CA002384407A CA2384407A CA2384407A1 CA 2384407 A1 CA2384407 A1 CA 2384407A1 CA 002384407 A CA002384407 A CA 002384407A CA 2384407 A CA2384407 A CA 2384407A CA 2384407 A1 CA2384407 A1 CA 2384407A1
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CA
Canada
Prior art keywords
azaadenine
guanine
cytosine
stability
oligonucleotides
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002384407A
Other languages
French (fr)
Other versions
CA2384407C (en
Inventor
Frank Seela
Helmut Rosemeyer
Enno Schweinberger
Dieter Heindl
Frank Bergmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Roche Diagnostics GmbH
Original Assignee
Roche Diagnostics Gmbh
Frank Seela
Helmut Rosemeyer
Enno Schweinberger
Dieter Heindl
Frank Bergmann
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Roche Diagnostics Gmbh, Frank Seela, Helmut Rosemeyer, Enno Schweinberger, Dieter Heindl, Frank Bergmann filed Critical Roche Diagnostics Gmbh
Publication of CA2384407A1 publication Critical patent/CA2384407A1/en
Application granted granted Critical
Publication of CA2384407C publication Critical patent/CA2384407C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/11—DNA or RNA fragments; Modified forms thereof; Non-coding nucleic acids having a biological activity
    • C12N15/113—Non-coding nucleic acids modulating the expression of genes, e.g. antisense oligonucleotides; Antisense DNA or RNA; Triplex- forming oligonucleotides; Catalytic nucleic acids, e.g. ribozymes; Nucleic acids used in co-suppression or gene silencing
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N2310/00—Structure or type of the nucleic acid
    • C12N2310/30—Chemical structure
    • C12N2310/33—Chemical structure of the base
    • C12N2310/333—Modified A
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
    • C12Q1/6813—Hybridisation assays

Abstract

Within oligonucleotides 2-azapurine and especially 2-azaadenine bases form specifically base pairs with guanine.
This base pair is of analogous stability as an adenine-thymine but less stable than a guanine-cytosine base pair. Therefore, the incorporation of 2-azaadenine residues into oligonucleotides instead of cytosine leads specifically to hybridization complexes with nucleic acids with homogenous stability. This is useful for the adaptation of the stabilities of different oligonucleotide sequences in all kinds of hybridization techniques, for example in oligomer chip technology.
CA002384407A 1999-08-30 2000-08-28 2-azapurine compounds and their use Expired - Lifetime CA2384407C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP99116767 1999-08-30
EP99116767.7 1999-08-30
PCT/EP2000/008371 WO2001016149A2 (en) 1999-08-30 2000-08-28 2-azapurine compounds and their use

Publications (2)

Publication Number Publication Date
CA2384407A1 true CA2384407A1 (en) 2001-03-08
CA2384407C CA2384407C (en) 2009-10-20

Family

ID=8238861

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002384407A Expired - Lifetime CA2384407C (en) 1999-08-30 2000-08-28 2-azapurine compounds and their use

Country Status (8)

Country Link
US (3) US7169553B1 (en)
EP (1) EP1214331B1 (en)
JP (1) JP4202646B2 (en)
AT (1) ATE342271T1 (en)
CA (1) CA2384407C (en)
DE (1) DE60031282T2 (en)
ES (1) ES2272322T3 (en)
WO (1) WO2001016149A2 (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE60031282T2 (en) 1999-08-30 2007-05-03 Roche Diagnostics Gmbh 2-AZAPURINE COMPOUNDS AND ITS USE
WO2003065146A2 (en) 2002-01-25 2003-08-07 Applera Corporation Methods for placing, accepting, and filling orders for products and services
WO2004007713A1 (en) * 2002-07-17 2004-01-22 Riken Nucleoside or nucleotide having novel unnatural base and utilization of the same
EP1658302B1 (en) 2003-07-25 2010-08-25 IDENIX Pharmaceuticals, Inc. Purine nucleoside analogues for treating diseases caused by flaviviridae including hepatitis c
US9677123B2 (en) 2006-03-15 2017-06-13 Siemens Healthcare Diagnostics Inc. Degenerate nucleobase analogs
EP2097436B1 (en) 2006-12-26 2012-02-01 Siemens Healthcare Diagnostics Inc. Heteropolynucleotide duplexes with purine-purine base pairing
EP2432796B1 (en) 2009-05-21 2016-08-17 Siemens Healthcare Diagnostics Inc. Universal tags with non-natural nucleobases
EP2875131B1 (en) 2012-07-18 2018-03-14 Siemens Healthcare Diagnostics Inc. A method of normalizing biological samples
EP2900681B1 (en) * 2012-09-28 2019-07-10 Ionovation GmbH Pharmaceutical composition comprising lipophilic nucleosides
DK2971098T3 (en) 2013-03-14 2019-02-18 Translate Bio Inc QUANTITATIVE ASSESSMENT FOR CAPE EFFECTIVENESS OF MESSENGER RNA
MX2015011944A (en) 2013-03-14 2015-12-01 Shire Human Genetic Therapies Quantitative assessment for cap efficiency of messenger rna.
US11597744B2 (en) 2017-06-30 2023-03-07 Sirius Therapeutics, Inc. Chiral phosphoramidite auxiliaries and methods of their use
AU2022284878A1 (en) 2021-06-04 2024-01-18 Translate Bio, Inc. Assay for quantitative assessment of mrna capping efficiency

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4458066A (en) 1980-02-29 1984-07-03 University Patents, Inc. Process for preparing polynucleotides
US4683202A (en) 1985-03-28 1987-07-28 Cetus Corporation Process for amplifying nucleic acid sequences
DE3739366A1 (en) 1987-04-10 1988-10-27 Boehringer Mannheim Gmbh DESAZA-PURIN-NUCLEOSIDE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE IN NUCLEIC ACID SEQUENCING AND AS AN ANTIVIRAL AGENT
DE3813278A1 (en) 1988-01-12 1989-07-20 Boehringer Mannheim Gmbh METHOD FOR DETECTING NUCLEIC ACIDS
US5143854A (en) 1989-06-07 1992-09-01 Affymax Technologies N.V. Large scale photolithographic solid phase synthesis of polypeptides and receptor binding screening thereof
DE3943522A1 (en) 1989-07-26 1991-02-07 Boehringer Mannheim Gmbh New aminoethoxy carboxylic acid derivs.
US5210015A (en) 1990-08-06 1993-05-11 Hoffman-La Roche Inc. Homogeneous assay system using the nuclease activity of a nucleic acid polymerase
DK51092D0 (en) 1991-05-24 1992-04-15 Ole Buchardt OLIGONUCLEOTIDE ANALOGUE DESCRIBED BY PEN, MONOMERIC SYNTHONES AND PROCEDURES FOR PREPARING THEREOF, AND APPLICATIONS THEREOF
DE4140463A1 (en) 1991-12-09 1993-06-17 Boehringer Mannheim Gmbh 2'-DESOXY-ISOGUANOSINE, THE ISOSTERAL ANALOGS AND THE APPLICATION THEREOF
DE4415370A1 (en) 1994-05-02 1995-11-09 Hoechst Ag Modified oligonucleotides, their preparation and their use
DE60031282T2 (en) 1999-08-30 2007-05-03 Roche Diagnostics Gmbh 2-AZAPURINE COMPOUNDS AND ITS USE

Also Published As

Publication number Publication date
WO2001016149A2 (en) 2001-03-08
WO2001016149A3 (en) 2001-08-02
US20090306360A1 (en) 2009-12-10
JP2003508405A (en) 2003-03-04
CA2384407C (en) 2009-10-20
ATE342271T1 (en) 2006-11-15
EP1214331B1 (en) 2006-10-11
US7847075B2 (en) 2010-12-07
DE60031282T2 (en) 2007-05-03
US7612187B2 (en) 2009-11-03
US20070015725A1 (en) 2007-01-18
US7169553B1 (en) 2007-01-30
ES2272322T3 (en) 2007-05-01
DE60031282D1 (en) 2006-11-23
EP1214331A2 (en) 2002-06-19
JP4202646B2 (en) 2008-12-24

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Effective date: 20200828